Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

254614

Sigma-Aldrich

N-(Phenylseleno)phthalimide

technical grade

Synonym(s):

2-(Phenylseleno)-1H-isoindole-1,3(2H)-dione, 2-Phenylselanylisoindole-1,3-dione, N-Phenylselenylphthalimide

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C14H9NO2Se
CAS Number:
71098-88-9
Molecular Weight:
302.19
MDL number:
MFCD00010406
UNSPSC Code:
12352100
PubChem Substance ID:
24855397
NACRES:
NA.22

grade

technical grade

Quality Level

100

mp

181-184 °C (lit.)

functional group

imide

storage temp.

−20°C

SMILES string

O=C1N([Se]c2ccccc2)C(=O)c3ccccc13

InChI

1S/C14H9NO2Se/c16-13-11-8-4-5-9-12(11)14(17)15(13)18-10-6-2-1-3-7-10/h1-9H

InChI key

TYZFQSLJTWPSDS-UHFFFAOYSA-N

Application

N-(Phenylseleno)phthalimide is a versatile selenamide reagent and has been used:
  • to selectively derivatize thiols for mass spectrometric analysis
  • to derivatize thiol peptides in protein digests
  • in L-prolinamide or pyrrolidine trifluoromethanesulfonamide promoted α-selenenylation reactions of aldehydes and ketones
  • for introducing PhSe into protected glycals, ketones, aldehydes, stannanes and exocyclic alkenes

Signal Word

Danger

Hazard Statements

H301 + H331,H373,H410

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKBD7898
MKBF2828
MKBG0394V
MKBG0394
MKBG3433V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Tetrahedron Letters, 34, 7755-7755 (1993)
Tetrahedron Letters, 33, 6243-6243 (1992)
Tetrahedron Letters, 34, 7915-7915 (1993)
Synlett, 419-419 (1992)
Jian Wang et al.
The Journal of organic chemistry, 70(14), 5678-5687 (2005-07-02)
[reaction: see text] A new catalytic method for direct alpha-selenenylation reactions of aldehydes and ketones has been developed. The results of exploratory studies have demonstrated that L-prolinamide is an effective catalyst for alpha-selenenylation reactions of aldehydes, whereas pyrrolidine trifluoromethanesulfonamide efficiently
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service